Winning Whitney
by Jebbs Cullen
Summary: Fox and Whitney are step-brother and sister. Whitney is a wild child and both their parents, after realising that Fox has feelings for her, agree that Fox would be good for her. They set off to Tobago where Fox hopes to win Whitney!


Chapter 1 : Miraflores

Fox was totally excited. He stood in the airport terminal at Piarco and contemplated his good fortune. How had he finally got to this point? After all the years of waiting, the years of pining, the years of self denial he was finally going to have a shot at a relationship with Whitney. As he sat in lobby area he peered over to where she was standing at the counter of Burger Boys ordering breakfast a breakfast he suspected she would eat then puke.

He wondered if she knew, if she had any inclination of what lay ahead. He had dreamt of this for so long had wanted it, wanted her for so long that he barely remember a memory, a thought before she was in his life. It was all irrelevant anyway, he would let her know how he felt. Let her know that he loved her not as a sister, let her know that he had never felt like her brother. He had been attracted to her from the moment she first spoke to him, well from their first conversation anyway. He would let her know how he felt, she would think about it and reciprocate his feelings. That's how it always happened at least every time he dreamt about it that was the way it happened.

His feelings for Whitney were so complex, so deep, so multi-faceted they were difficult to put into words. Even in his mind when he thought about how and what he felt he found it difficult to express. How does one express feelings of love so absolute, so inextricably bound up in familial protectiveness, in what seemed like a lifetime of hidden desire, in unrequited yearning? He could readily admit to himself that his feelings had their genesis in sexual desire, lust of the basest kind. But that was expected given their earliest encounters. Whitney had shocked him with the frank manner of speaking particularly as a fourteen year old. He had been drawn in by her spirit and vivacity, by her bluntness. It is not often that one encounters a fourteen year old, let alone a fourteen year old girl, who openly talks about her sexual encounters with her teachers and classmates.

The sound of her distinctive chuckle drew him out of his reverie. When his eyes regained focus he noticed that she was flirting with a man who looked to be at least two decades older than she was. He was dressed in what appeared to be pilot's uniform no less. Leave it to Whitney to attract the pilot away from his preparations for his early morning flight.

He knew that laugh anywhere and he knew what it meant, she was flirting with someone she was actually interested in. He had made a study of her. Fox had been observing her for the better part of three years now and he would have been able to tell what she was up to even if there were a brick wall between them. She had separate laughs for separate situations. One for when she flirted with a guy who she would never let get to first base, one for a guy who she felt who only warrant a one night stand and another for a guy who she thought she might allow to screw her more than once. This guy she would give a second screw. He had to nip it in the bud.

The choice was clear. He could not sit by and allow her to consummate this flirt. He knew that if he left her alone she would soon be joining the mile high club or worse yet the airport bathroom club. He wouldn't allow that to happen not now when he was so close, not when he had his eye on the proverbial prize. He had to get her to the villa without any new phone numbers. Her little black book had long ago lost the right to be called little.

Fox got up slowly and planned what he would say. She had no idea of what was about to unfold in Tobago and he wanted to keep it that way. He couldn't let his feelings slip now. He had kept them under wraps for so long, he could do it for a few more hours. He approached the counter and noticed that he had caught the attention of the sales clerk. Strange what love could do, there was a time when he would have jumped at the opportunity to flirt with the clerk perhaps get her number but alas no more. He only saw Whitney now, had seen only her for the last three years. AS he approached them he overheard the pilot say:

"Well what do you like to do then? If reading is so boring how does an angel like you spend your time?" Fox overheard the pilot say

"Well I enjoy getting and giving …" Whitney answered with one eyebrow raised

"Getting and giving what Whitney?" Fox interrupted

"Backrubs, … I was about to say backrubs," she answered testily. Whitney slowly looked away from the pilot and took in Fox with an expression that screamed 'Why are you interrupting me!'

He knew that she wanted to tell him off but her upbringing would not allow her to do it in public. She would never be part of such a public scene.

"Fox, this is um.."

"Jack …Jack Trent. And you are?"

So the old perv had a name, one which they apparently hadn't exchanged yet. That was good he had got to them in time, before much damage could be done. Fox contemplated his reply. He wanted to say 'the guy who protects her from pedophiles' but knew that that answer might raise a hornet's nest and not one from the pilot. So instead he relied on old faithful.

"I'm her older brother"

Fox hated having to refer to himself as her brother especially now when he wanted to change the nature of their relationship. The label was wearing thin but what else could he have said 'her boyfriend', 'her lover'. He certainly was none of those things to her. Not yet anyway not until he declared himself in Tobago.

Old faithful did the trick.

"Oh well I was just saying hello, um… to your sister here. Just ensuring that all passengers enjoy their stay at the um… airport. Well I'll see you two onboard! Enjoy the flight."

Fox's eyes followed the pilot as he beat a hasty retreat; out of the lobby, down the corridor and into what Fox could only presume was the pilot's lounge.

"What the fuck was that all about Fox? Can't I talk to the pilot?"

"Please Whitney, the guy is probably in his thirties! Are you that desperate?"

"We can't all be pillars of virtue like you Fox. Besides he was really cute and I bet he has a huge dick"

"Don't be crude Whitney! Is that all you ever think of?"

"Do you even hear yourself?" Whitney screwed up her face "Yes, it is all that me and the rest of the ordinary warm blooded people think of! Why don't you get a life Fox? Better yet, why don't you go get laid and stop cockblocking?"

He couldn't he tell that her was cockblocking so that he _would_ have a chance to get laid … by her?

"I'm just saving you from yourself Whit. They haven't found a cure for AIDS yet, in case you haven't heard!"

Whitney just sighed and rolled her eyes.

"All passengers for BW1504 departing to Crown Point Airport at 5:40 a.m. Now boarding at Gate 2"

The call came over the public announcement system. Whitney and Fox picked up their respective pieces of hand luggage and headed down the stairs toward the relevant gate. They walked the rest of the way to the plane in silence.

As the pair walked across the terminal foyer Fox slowed his step and allowed Whitney to get slightly ahead of him. He took the opportunity to take her in fully. The denim dress she wore showed off her curves without clinging. Its delicate floral pattern setting off the pearl necklace and simple pearl drop earrings that she wore. As usual she wore sensible shoes, a pair of denim espadrilles. The shoes allowed her to walk freely and he was in the perfect location to enjoy that freedom. Fox enjoyed looking at Whit's derriere. Its motion always amazed him, always pleased, always aroused him as it was doing now. He quickened his pace until he caught up with her. He could not allow himself to become too aroused, briefs could only do so much.

This was going to be the longest 15 minute flight he'd ever taken.

…..

The villa he had booked was 20 minutes from the Crown Point airport. They drove in silence enjoying the scenic route. Once at the villa they quickly devoured their complimentary welcome drinks which were served to them at the door by one of the villa's maids.

"Fox Crane and Whitney Russel" Fox announced to the maid

"Pleased to meet you sir, and … er madam. I'm Sharon, one of the maids at Miraflores Villa."

Fox could tell that she was slightly surprised at Whitney's age. What was a teenager doing holidaying in a villa with a man who appeared to be at least five years older than she was? He was sure that she was running through all sorts of scenarios in her mind. A smile played on his lips. Let her think what she would, he certainly was not about to correct her not when he himself hoped that her worst suspicions would later be confirmed.

He chose instead to focus on the villa that would be their home or the nxt month. He had chosen the villa for its secluded location. It sat high up on the end of a small sandy cove and it would be easy to enjoy open and sweeping dramatic views across the ocean from most of the villas rooms. The villa came staffed with 2 maids, a cook and a night watchman. The small staff made it easily a location at which one could experience secluded privacy while still enjoying the creature comforts of life.

The villa was a 4 bedroom, 5 bathroom home, totally unlike any other property on the little island of Tobago. Its living room was open to the bay, and one could easily wind down the cream canvas shutters to provide shade for the huge teak day beds. There were also 4 teak upright arm chairs and a large coffee table. He had also chosen the villa because at this time of the year the villas annual 'repair and renovation' programme meant that 3 of its four bedrooms were closed for the season.

"Let me show you to your room"; Sharon said as she lead the pair to the master bedroom which was the only bedroom that remained open.

On the way to the bedroom they passed a well appointed kitchen which was open and breezy with two large ceiling fans and Demerara widows on sticks which open to give a view of the perfect beach below. It was fully equipped with double door stainless steel fridge with a filtered water and ice making facility, a large stainless steel gas cooker and a dishwasher. To one side of the room was an open air barbecue area and on the other a pantry and utility room with washer and dryer.

Around the corner was the master bedroom. They placed their luggage on the floor in front of the built-ins. They knew that once they left the room this morning, it would be packed away for them. Looking around the master bedroom and bathroom he noticed that there were shuttered windows that opened out so that it would be easy to shower, have a bath or lounge in the teak four poster bed while watching pelicans fish in the turquoise Atlantic. There was also a desk with a dedicated internet connection which was positioned to give its user views over the deep infinity pool to the gazebo and beyond.

Whitney seemed surprised about something. He knew she would let him have it once they were alone so he braced himself for it. Sharon departed after the requisite 'if there's nothing else I can get for you sir, madam, I'll leave you two alone'

Once the doors were closed Whit began horrified:

"Are we sharing a room Fox? Why didn't you get two rooms? If you think I'm not going to have sex while we're here you have another thought coming! You'll just have to leave the room whenever I bring someone over."

"Take a breath Whit. One, the other rooms are closed for the season and two, don't forget that the reason we're here is so that you can take a break from the random hook-ups Whit. It's not healthy. You're only sixteen you need to slow down."

"And you're only 22 you need to stop acting like my surrogate father. I, unlike you, know that I'll only be young once and I intend to make the most of it."

"Making the most of it doesn't mean screwing everything in pants."

"I don't screw everything in pants. I happen to have very discerning tastes. I haven't screwed you now have I?"

Where did that come from? Did she know? Did she suspect what he had been feeling, did she know what he intended to reveal on this trip? She couldn't, he had been very careful over the years, but then again Mom and T.C. had figured it out hadn't they? Why not Whitney? Still, her facial expression suggested that she had just said that to tease him. He so wanted to walk over to her and tell her that she may not have screwed him yet but he hoped that that would change in the next few days or hours. Instead he said;

"Ha ha, you should be so lucky!"

Whitney just sighed and rolled her eyes again signalling the end of the discussion. It always amazed him how they could discuss things without arguing. There were never raised voices or hurt feelings at the end of their talks no matter how controversial the issue or how different their opinions on the subject matter. He cherished that aspect of their relationship and hoped that it would survive his revelations.

As if on cue they both headed over to the shuttered folding doors which opened up to the wooden deck that surrounded their room. Immediately in front of the deck was the coy pond. Green lily pads and purple water plants floated on it and the construction of the villa gave the illusion that the house itself was also floating on the pond.

A short walk along the deck lead to the covered outdoor area which included an outdoor dining area and courtyard barbecue area immediately beyond which was the infinity pool, Jacuzzi and gazebo.

"How about a skinny dip?"

"Whit! Its 10 o'clock in the morning!"

"So? No one would see us but the staff, and I'm sure they've seen plenty worse. We have the house, and it seems the entire cove, to ourselves, so why not make the most of it?"

As she spoke Whitney took off her shoes and put her toes in the water as if to test the temperature. Of course it would be perfect the sun was shining brilliantly and there were very few clouds in the sky so that the pool would be perfectly heated. Fox watched as she began tugging at the zippier of her thin strapped denim dress. When she found she couldn't get it undone herself she turned her back to Fox.

He held on to her zipper with his left hand and placed his right hand on her bare shoulder. As he pulled her zipper down ever so slowly, he used the opportunity to caress her shoulder with his hand. Her ebony skin was soft, as smooth as silk and tender to his touch. As the zipper reached the middle of his back he was pleasantly surprised to find that she was not wearing a bra. He knew that had not seen any strap but had presumed that she wore a strapless bra. Her breasts had seemed so perky in the dress. He now guessed that they were naturally perky. He couldn't wait to taste them.

Fox moved the zipper further down her back he began to anticipate, no to hope, that she had decided not to wear any undergarments at all. Lower and lower the zip moved until all his hopes materialized. He gazed at her perfect round bare backside and felt his member begin to twitch. He needed to sit down quickly before he embarrassed himself.

He left her just as the dress slid down to her ankles. Fox walked across to the to the wooden beach lounge chair with its long cushion covered in crisp lime green and white stripes and just as he sat down he heard Whitney ask from the edge of the pool:

"Aren't you going to join me?"

"Nah, I'll sit this one out." The view would be better form up here anyway.

"What are _you_ shy, Fox? I thought all Crane men were bold!"

"No, but I wouldn't want to shock you. You are accustomed to playing with little boys after all."

"Ha Ha. Very funny Fox. Are you trying to insinuate that your cock is larger than any I've ever had?

"Not insinuating, stating." He calmly replied

"Well if you're so confident why don't you show me" She said raising one eyebrow so that her dare was plainly written across her lovely face. "Come join me, don't let me bathe here all by my lonesome," she pouted. She had obviously decided to switch tactics when she realised that the dare had not worked.

" I said no Whitney" He insisted. He could ill afford to get up now and she had not even moved away from the side of the pool. The anticipation of what he was about to see was enough.

"Ok, spoil sport. Well, since you're not joining me could you get me my towel please?"

"You should have thought of that before you stripped your clothes off and got into the pool."

"Are you or are you not going to get it for me?" She asked

"Not" By this time he really could not move plus he knew that he'd relish the sight of her walking naked in front of him. Why should he deny himself that pleasure? He'd been a martyr for far too long!

He watched push off the edge of the pool in a perfect butterfly stroke and noticed for the first time that she was clean shaven. He had thought that he couldn't get any harder but the sight of her bare, bald pussy proved him wrong. He wriggled in his seat to give himself more room.

He sat and watched her make several laps, always pretending to be distracted by something else. The water cascaded over her long lithe body. All those years of tennis practice really showed. She was the picture of feminine perfection. She wore her hair natural and its short twists which usually framed her face perfectly were now slick and heavy with water.

_Twenty minutes later, Fox watched as she emerged from the pool. _

"_You asked for it Fox" she said as she raised herself out of the water. _

_Each step on the stair revealed more of her deliciously naked glory. Instead of heading toward the house, He noticed that she was making a b-line for him. He adjusted himself in the lounger, sitting upright this time. Whitney strutted seductively over to him, turned around and said,_

" _Is this what you wanted big boy"_

_He couldn't believe it. A deep groan escaped his lips as she turned around and sat on his lap. Fox held on to the lounge chair for dear life. Whitney gyrated and swayed her hips against his erection. When he could stand it no more he whispered in her ear,_

"_Turn around please"_

_Whitney got up and turned around. As she sat back down he held on to her hips as if to signal that she should continue as before. She took the cue and began dancing against him. His head rolled back and he let go of her hips and reached instead for her supple breasts. He brought first one and then the other nipple to his mouth. She tasted divine! Just as he was about to reach down and free his member so that he could fully enjoy her motions…_

He felt a splash of cold water on his shirt. It snapped him out of his daydream.

"That's for not bringing my towel for me" Whitney declared as she walked away. Well at least now he would be able to walk back to the house!


End file.
